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Got my first contract!

He just brought the papers into me, signed. It was a place I really wanted, butts up to our property. He said its too cheap though, and he tells me what they used to pay the last guy, but IMO, the last guy was a little carried away, its a 15min job, they were paying $750/yr. I charged $500, based on 10 plows. Oh well, this was my first real bid, so thats the price you pay for being a rookie.
Im just glad I got it. Next year, +100.

Congratulations. My advice in a situation like that is to accept his "help" graciously. He realizes you're new (even if you didn't tell him) and is wanting to feel superior. Let him, as long as it benefits you. Tell him you appreciate the extra $100 or whatever he offers. Take a lesson and go up on your estimates.

Congrats I remember our first contracts stress full couple of months but as long as you do good work they keep coming back no mater what your price is (with in reason) allot of our contracts were not the lowest price but our costumers keep coming back because they are happy with the service and cant justify saving some money to get some one else. Keep him happy and his mouth will be the biggest billboard you can buy plus its free. Good luck

Congrats on your new contract! Just like everybody else said...prove to them that they won't EVER need anybody else. Especially on seasonal contracts, keep in close contact with the property owner throughout the season to make sure they are happy with how you are performing...it'll go a long way!